Fractional VP of Delivery · Atlanta, working nationally

One plan for IT and Product. Built for the AI era.

Most companies have a leader for what gets built and a leader for how it gets built. Very few have anyone who owns whether the two actually deliver together. That's the seat I fill, without the cost of a full-time executive hire.

I report to the outcome, not to either side.
  • SAFe Program Consultant (SPC6)
  • Former Director of Application Integration
  • Solution Train Engineer & Release Train Engineer
  • Developer turned delivery executive, still building with AI

The problem I solve

When IT and Product aren't aligned, the symptoms are familiar.

  • Product says engineering doesn't deliver what was asked for.
  • IT says Product keeps changing direction.
  • Several PMOs report different versions of the truth. Status stays green until it suddenly turns red.
  • Delivery teams take direction from everyone and work from no single plan.

AI has made this gap more expensive. Coding tools let teams build faster than IT and Product can agree on what to build. When an AI agent works from a vague requirement, its guess becomes working code across several teams before anyone notices they read it differently.

The risk isn't only building the wrong thing. It's building the wrong thing faster, across multiple teams.

What clients get

Five things that change when someone owns delivery across both sides.

  1. One plan IT and Product both commit to

    A single planning rhythm where trade-offs surface early and are decided with evidence, not escalation.

  2. One version of the truth

    PMO reporting brought together into one set of predictability, flow and outcome metrics leaders trust.

  3. A specification practice built for AI

    Living, testable specifications that evolve with the code, so teams and AI tools build from the same clear intent.

  4. Deeper stakeholder collaboration

    The business shapes what's built throughout the quarter, not just at the final demo.

  5. Capability that stays

    I coach delivery leaders, Scrum Masters, Product Owners and program managers, and develop a permanent successor.

How I work

Iterate the specification, not just the code.

For two decades Agile taught teams to iterate the code. Now that AI can generate code quickly, the most valuable place to iterate is upstream, on the specification. And the specification is exactly where IT and Product have to meet.

This is not a return to waterfall. Waterfall froze the specification behind approval gates. In my approach the specification and the code evolve together, and real user feedback is allowed to change both.

The living specification loop

Intended behavior, verified code and observed outcomes have to agree. When correct code misses the business need, the learning goes back to intent.

  1. 01IntentGoals and guardrails from IT and Product
  2. 02ExamplesStakeholders approve concrete scenarios
  3. 03Testable specAcceptance criteria, constraints, interfaces
  4. 04Build with AIDevelopers review output against the spec
  5. 05VerifyTests trace back to the criteria
  6. 06Release & learnReal outcomes feed the next round of intent

Offered as a lean 90-day pilot: one existing team, two features already planned, the tools and ceremonies you already have, and compared against that team's own recent history. Clear stop-or-scale decision points along the way.

How planning changes for AI-assisted teams
AreaTraditional approachMy approach
ReadinessIs the work sized and small enough?Is it testable? Clear acceptance criteria, constraints and interfaces before anyone builds.
DependenciesTeam A needs something from Team B by a date.Teams agree on the behavior between their systems, who owns it and when they'll test it together.
CapacityFaster coding means more committed scope.Review, integration, security and business validation are planned as real constraints.
DoneThe code passes its tests.Specification and code stay aligned, and the result is validated with real users.
ReviewCheck that the work matches the plan.Study whether the outcome solved the business problem, and adjust both if it didn't.

Engagement options

Start small, prove value, then decide.

Start here

Delivery Alignment Diagnostic

2–3 weeks · fixed scope

I interview the VP of IT, the VP of Product, PMO leaders and people across delivery, observe a planning cycle, and review intake, backlog and status artifacts.

You receive an executive readout, the cost of misalignment in your own numbers, and a 90-day roadmap with the top three changes.

Discuss a diagnostic

Fractional VP of Delivery

Typically 3–6 months · part-time

I own the delivery operating model across IT, Product and the PMOs: one forum for trade-off decisions, quarterly planning and review, the specification practice, unified executive reporting and coaching for delivery leaders.

AI-Era Delivery Pilot

One team · 90 days

A controlled trial of the living specification loop on features that span IT and Product, measured on first-pass acceptance, rework, blocking questions caught early and change failure rate.

Program Rescue

Time-boxed

For a program already in trouble: stabilize the delivery rhythm, unify fragmented backlogs, map cross-team dependencies and restore executive confidence.

Sponsors

CIOs, CTOs and CEOs tired of breaking the tie between IT and Product.

Partners

VPs of IT, Product and Engineering, and PMO leaders.

Organizations

Mid-market and enterprise companies with multiple teams, often more than one PMO, often adopting AI coding tools. SAFe helps but isn't required.

Industries

Financial services, health insurance and healthcare, property and casualty insurance, aerospace and defense, logistics and B2B integration.

Selected results

Delivery outcomes from real programs.

First Advantage

45%

increase in IT Operations delivery over 18 months.

As Release Train Engineer for three trains and 12 cross-functional teams spanning Salesforce, AWS call-center and mobile work, I mapped the value streams, established the PMO process and unified the customer request backlog into one intake funnel.

CareSource

35%

less blocked work

A biweekly planning mechanism ended recurring War Room escalations. A Shared Services intake process now governs demand across EDI, ESB, D365 and OnBase.

Rollins

600 / 700

backlog items cleared in six months

A maintenance-system recovery delivered for $190K against a $250K budget.

Osaic, consulting through Equillem

+2

workstreams approved

Stabilized an inherited modernization program. My discovery work identified 12+ integration gaps that shaped a new modernization engagement.

Catlin

$77M

Guidewire transformation

Built and led the integration team connecting legacy applications worldwide to Guidewire through an enterprise service bus, with follow-the-sun delivery.

Synchrony

12 teams

100+ people in transformation

Coached one RTE, six Scrum Masters and six Product Owners. Also coached transformations at Verizon Telematics and Anthem, and mentored release train leaders at Cigna.

Why me

I've been on every side of delivery.

I've spent much of my career between the VP of IT and the VP of Product, coordinating the delivery teams and PMOs that serve them both. I still build software today with AI, so my advice stays grounded in what engineers actually face.

Portrait of Robert Jackson
Robert JacksonFractional VP of Delivery · Atlanta
  1. Builder

    Developer and integration engineer across ERP, EDI and enterprise integration. I know what it's like to get a vague requirement and have to guess.

  2. Technology executive

    Director of Application Integration at Rollins: 14 direct reports including managers and business analysts, multimillion-dollar budgets, special projects for the CIO.

  3. Enterprise delivery leader

    Solution Train Engineer at Cigna. Release Train Engineer at CareSource, First Advantage, Lockheed Martin (contract) and Osaic.

  4. Fractional VP of Delivery

    Bringing that whole path to organizations that need an experienced delivery executive, but not a full-time hire.

Credentials

  • SAFe Program Consultant (SPC6), qualified to train and certify leaders and teams
  • Additional SAFe and Agile certifications, including SAFe Scrum Master, which I teach
  • BBA, Management Information Systems, University of Georgia
  • IT Management Program, Georgia Institute of Technology

Are your IT and Product leaders working from different plans?

Or did output go up after AI while outcomes didn't? Let's talk it through. Thirty minutes, no pitch deck.